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Resolution of oxiranes. Application to the synthesis of the platelet aggregation factor

✍ Scribed by Bernard Cimetiere; Laurent Jacob; Marc Julia

Publisher
Elsevier Science
Year
1986
Tongue
French
Weight
172 KB
Volume
27
Category
Article
ISSN
0040-4039

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✦ Synopsis

Resolution of racemic oxiranes has been achieved through their conversion into hydroxy sulfonium salts of dibenzoyltartaric acid. Thus, resolution of n-octadecyl glycidyl ether followed by reaction with phosphorylcholine and acetylation led to CIB-P.A.F.

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## Abstract Treatment of phenyl 2,3,6,2β€²,3′‐penta‐__O__‐benzoyl‐1‐thio‐β‐D‐lactoside (7) with BF~3~ in methyl pyruvate afforded the corresponding phenyl 4β€²,6′‐__O__‐[(__R__)‐1‐(methoxycarbonyl)ethylidene]‐1‐thio‐β‐D‐lactoside (9) in 91% yield. The latter was converted via bromide 10 into the corres